Dimethylformamide → HCID 66990931、化合物

HRID 2367357

反応式

HRID 2367357 の反応式
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH:16]([C:20]([OH:22])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C=O)C.C(N(CC)CC)C.[NH2:35][CH2:36][C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1)=[O:38]>C(Cl)Cl.O>[Cl:45][C:41]1[CH:40]=[C:39]([C:37](=[O:38])[CH2:36][NH:35][C:20]([CH:16]2[O:17][CH2:18][CH2:19][N:14]([CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:15]2)=[O:22])[CH:44]=[CH:43][CH:42]=1

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27763534-Benzylmorpholine-2-carboxylic acidHCID 3026272HCID 3026272、化合物

生成物 1

HCID 66990931HCID 66990931、化合物収率 21.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

Oxalyl chloride (1.32 mL, 15.03 mmol) was added to the suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (2.218 g, 10.02 mmol) and DMF (0.155 mL, 2.005 mmol) in CH2Cl2 (100 mL) at 0° C. in 10 minutes, and the resulting mixture was stirred at 25° C. for 2 hours. The mixture was concentrated, and the resulting residue was dissolved in CH2Cl2 (100 mL) and triethylamine (3.07 mL, 22.05 mmol). 2-Amino-1-(3-chlorophenyl)ethanone (1.7 g, 10.02 mmol) was added to the brown solution at 0° C., and the reaction mixture was stirred at 25° C. for 3 hours. Water (150 mL) was added to the reaction mixture, and the aqueous mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated. The resulting residue was purified by silica gel chromatography using as eluent 50% EtOAc in petroleum ether to afford the title compound (800 mg) as a pale yellow solid. LC-MS (ES) m/z=373 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (100 mL)
  3. stirringthe reaction mixture was stirred at 25° C. for 3 hours
  4. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-dc534dcd9e8b4cacba077eac4215afda
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

関連ノート

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